Literature DB >> 19156653

Organocatalytic asymmetric alkylation of aldehydes by S(N)1-type reaction of alcohols.

Pier Giorgio Cozzi1, Fides Benfatti, Luca Zoli.   

Abstract

Work-alcoholic! The elusive enantioselective catalytic alpha-alkylation of aldehydes, a widely sought transformation, was brought to execution by the use of alcohols capable of forming stabilized carbocations (see scheme, TFA = trifluoroacetic acid).

Entities:  

Year:  2009        PMID： 19156653     DOI： 10.1002/anie.200805423

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  12 in total

1.  Chiral Brønsted base-promoted nitroalkane alkylation: enantioselective synthesis of sec-alkyl-3-substituted indoles.

Authors:  Mark C Dobish; Jeffrey N Johnston
Journal:  Org Lett       Date:  2010-11-19       Impact factor: 6.005

2.  Spin-Center Shift-Enabled Direct Enantioselective α-Benzylation of Aldehydes with Alcohols.

Authors:  Eric D Nacsa; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2018-02-22       Impact factor: 15.419

3.  Enantioselective α-benzylation of aldehydes via photoredox organocatalysis.

Authors:  Hui-Wen Shih; Mark N Vander Wal; Rebecca L Grange; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2010-10-06       Impact factor: 15.419

4.  Enantioselective catalytic alpha-alkylation of aldehydes via an SN1 pathway.

Authors:  Adam R Brown; Wen-Hsin Kuo; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2010-07-14       Impact factor: 15.419

5.  Synergistic Catalysis: A Powerful Synthetic Strategy for New Reaction Development.

Authors:  Anna E Allen; David W C Macmillan
Journal:  Chem Sci       Date:  2012-01-25       Impact factor: 9.825

6.  Transition states and origins of 1,4-asymmetric induction in alkylations of 2,2,6-trialkylpiperidine enamines.

Authors:  Joann M Um; Naeem S Kaka; David M Hodgson; K N Houk
Journal:  Chemistry       Date:  2010-06-01       Impact factor: 5.236

7.  Palladium-catalyzed, pyrrolidine-mediated arylmethylation of ketones and aldehydes with coumarinyl(methyl) acetates.

Authors:  Kalicharan Cattopadhyay; Antonio Recio; Jon A Tunge
Journal:  Org Biomol Chem       Date:  2012-07-25       Impact factor: 3.876

8.  tert-Butyl 3-benzyl-3-[(E)-2-benzyl-idene-3-oxocyclo-pent-yl]-2-oxoindoline-1-carboxyl-ate.

Authors:  Zhen Qiao; Li Liu; Dong Wang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-03-12

9.  Enantioselective Formal α-Methylation and α-Benzylation of Aldehydes by Means of Photo-organocatalysis.

Authors:  Giacomo Filippini; Mattia Silvi; Paolo Melchiorre
Journal:  Angew Chem Int Ed Engl       Date:  2017-03-21       Impact factor: 15.336

10.  Stereocontrolled synthesis and functionalization of cyclobutanes and cyclobutanones.

Authors:  Francesco Secci; Angelo Frongia; Pier Paolo Piras
Journal:  Molecules       Date:  2013-12-13       Impact factor: 4.411
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